According to reporting by The Information, Anthropic takes a stricter stance than OpenAI when enterprise customers reach their contracted token limits. Once customers burn through the tokens covered by their agreements, Anthropic removes their discounts and charges standard rates, sources told The Information on Monday. OpenAI, by contrast, operates with considerably more flexibility in these situations.
Managers at software companies who purchase from both vendors described Anthropic's discounts as hovering around 15% below list price. When those discounted tokens run out, customers face a choice: negotiate a new contract or accept full pricing. Tokens represent the billing unit that AI companies use to charge for text processed and generated by their models.
OpenAI's more lenient approach
A software licensing consultant familiar with both companies explained to The Information that OpenAI handles token exhaustion differently. The company permits customers to continue operating under their existing discount through the remainder of the current month, plus an additional full month to finalize a fresh contract. Only after this two-month window expires do standard list prices kick in.
Traditional cloud infrastructure providers—Amazon, Microsoft and Google—operate under yet another model. According to Jeff Muscarella, chief innovation officer at NPIFinancial, these companies typically allow customers to maintain their negotiated discount rate on usage that exceeds their commitment level for the duration of the contract.
Frederick Philipson, co-founder of Redress Compliance, told The Information that OpenAI is currently pursuing enterprise deals more aggressively than Anthropic, particularly through pricing incentives. This shift coincides with OpenAI's recent hiring of its first global sales chief this month.
A major customer defects
The stricter terms may already be affecting Anthropic's customer retention. Harjot Gill, chief executive of CodeRabbit, disclosed to The Information that OpenAI has become his company's primary AI vendor, replacing Anthropic in that role six months earlier. CodeRabbit, which is three years old, spends tens of millions annually on AI services.
Both Gill and another manager noted that Anthropic and OpenAI have begun inserting "share of wallet" provisions into their discount agreements. These clauses mandate that large customers direct the majority of their AI spending toward a single platform.
The Information's reporting indicates that over 100 companies spent more than $10 million annually with Anthropic during the 12-month period ending in June, while more than 1,000 companies spent over $1 million. Meta and Cursor rank among Anthropic's most significant customers.
Despite these contractual challenges, Anthropic achieved a milestone last quarter by surpassing OpenAI in revenue for the first time. Both companies have recently adjusted their pricing downward, with Anthropic introducing a less expensive version of Opus and OpenAI cutting GPT-6 prices in half.
Source: The Next Web
